((2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-((2R,3S)-2-vinyl-tetrahydro-pyran-3-yloxy)-silane

Base Information

Chemical Name:((2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-((2R,3S)-2-vinyl-tetrahydro-pyran-3-yloxy)-silane
CAS No.:485386-55-8
Molecular Formula:C₃₁H₄₂O₇Si
Molecular Weight:554.756
Hs Code.:

Synonyms:((2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-((2R,3S)-2-vinyl-tetrahydro-pyran-3-yloxy)-silane

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Chemical Property of ((2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-((2R,3S)-2-vinyl-tetrahydro-pyran-3-yloxy)-silane

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Technology Process of ((2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-((2R,3S)-2-vinyl-tetrahydro-pyran-3-yloxy)-silane

There total 5 articles about ((2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-((2R,3S)-2-vinyl-tetrahydro-pyran-3-yloxy)-silane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 67.0%

: 75-78-5,30107-43-8
dimethylsilicon dichloride

: 101208-75-7
(2R,3S)-2-vinyltetrahydro-2H-pyran-3-ol

: 236424-93-4
methyl 2,3-di-O-benzyl-6,7-dideoxy-α-D-gluco-hept-6-enopyranoside

: 485386-55-8
((2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-((2R,3S)-2-vinyl-tetrahydro-pyran-3-yloxy)-silane

Guidance literature:: methyl 2,3-di-O-benzyl-6,7-dideoxy-α-D-gluco-hept-6-enopyranoside; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

dimethylsilicon dichloride; at -78 - 20 ℃; for 3h;

(2R,3S)-2-vinyltetrahydro-2H-pyran-3-ol; With 1H-imidazole; In tetrahydrofuran; at 20 ℃; for 13h;
DOI:10.1016/S0040-4039(02)01617-9

Reference yield:

: 118545-10-1
(2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-tetrahydro-pyran

: 485386-55-8
((2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-((2R,3S)-2-vinyl-tetrahydro-pyran-3-yloxy)-silane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 95 percent / CSA / methanol / 0 °C

2.1: 77 percent / TBAF

3.1: nBuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C

3.2: 3 h / -78 - 20 °C

3.3: 67 percent / imidazole / tetrahydrofuran / 13 h / 20 °C

With n-butyllithium; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; hexane; 2.1: Swern oxidation;
DOI:10.1016/S0040-4039(02)01617-9

Reference yield:

: 305815-34-3
[(2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-methanol

: 485386-55-8
((2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-((2R,3S)-2-vinyl-tetrahydro-pyran-3-yloxy)-silane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 77 percent / TBAF

2.1: nBuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C

2.2: 3 h / -78 - 20 °C

2.3: 67 percent / imidazole / tetrahydrofuran / 13 h / 20 °C

With n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; 1.1: Swern oxidation;
DOI:10.1016/S0040-4039(02)01617-9